Upcoming Events

Slide into the spirit of summer with us on Fridays, June 6, 13, and 27, and Saturday, June 21, from 3–6 PM. Partake in sun-drenched afternoons with live music, sweeping waterfront views, tasty bites, and crisp, refreshing beverages. The carefree rhythm of summer starts now!

Rain, Rain, Go Away… We’re Paws-ing ‘til a Brighter Day!  Due to the forecast,  Paws & Plates has been rescheduled to Wednesday, June 18. Same location, same pup-approved fun!

Join us for Paws & Plates, a dog-friendly evening at the Lighthouse on the Pointe, welcoming locals and visitors alike from 4 to 7 pm. Bring your pup and enjoy live music, our pizza oven, and a wine and beer bar, all while supporting a great cause: 10% of proceeds will benefit Talbot Humane Society. Don’t miss the doggie menu and pop-up shop filled with treats and toys for your four-legged friend!

Celebrate Memorial Day weekend with us! Start Friday with live music on the Waterside Lawn from 3 to 6 PM. On Saturday, enjoy an elevated poolside experience with a special menu by The Botanist, available from 12 to 3 PM. Then on Sunday, head waterside from 11:30 AM to 2:30 PM for live music, grilled favorites, our pizza oven, and wine cart!

Plan ahead for the 37th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum, happening June 13–15! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Visit here for event details and highlights.

Join us for Fourth of July and enjoy front row seats to the St. Michaels' stunning fireworks display on Saturday, July 5th.

Plein Air Easton, celebrating its 21st year July 11 - 20 2025, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.

Mark your calendars for August 10th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen. 

The prestigious Chesapeake Film Festival returns to Easton, Maryland from October 10th - 12th! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought-provoking documentaries, and engaging discussions with industry experts.

Fall into the enchantment of St. Michaels October 17 - 19! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.

Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 25th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!

Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 14th - 16th! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!

Mark your calendar for November 22nd, as the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, hosts the Holiday Edition of the beloved Sea Glass and Coastal Arts Festival. This seasonal celebration will showcase coastal craftsmanship at its finest, with over 90 exhibitors offering unique jewelry, home décor, art, and more—just in time for the holidays.